Hui Gao

Hui Gao
Guangzhou Medical University | gzhmc · School of Pharmaceutical Sciences

PhD

About

58
Publications
4,932
Reads
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1,350
Citations
Citations since 2016
41 Research Items
1221 Citations
2016201720182019202020212022050100150200250300
2016201720182019202020212022050100150200250300
2016201720182019202020212022050100150200250300
2016201720182019202020212022050100150200250300
Introduction
Mechanisms for organic synthesis reaction; Computer-aided drug design; Quantum & Theoretical chemistry
Additional affiliations
March 2018 - April 2020
Guangzhou Medical University
Position
  • Professor
Description
  • Mechanisms for organic synthesis reaction; Rational catalyst design & Computer-aided drug design; Quantum & Theoretical chemistry
June 2016 - February 2018
Sun Yat-Sen University
Position
  • Researcher
Description
  • Mechanisms for organic synthesis reaction
July 2011 - May 2016
Guangzhou Institute of Energy Conversion,Chinese Academy of Sciences
Position
  • Professor (Assistant)
Description
  • Rational catalyst design; Quantum & Theoretical chemistry
Education
September 2006 - June 2011
Sun Yat-Sen University
Field of study
  • Quantum & Theoretical chemistry
September 2002 - June 2006
Shanxi University
Field of study
  • Chemistry

Publications

Publications (58)
Article
By developing gem-difluoromethylene allenes as viable partners, regiocontrolled Rh(III)-catalyzed redox-neutral C-C coupling/C-N cyclization has been realized to build the pyridin-2(1H)-one motifs with the embedment of a Z-configured monofluoroalkene functionality, in which either (hetero)aromatic or vinylic amides were found to be compatible. Inte...
Article
The Rh(III)-catalyzed chemo-, regio- and stereoselective carboamination of sulfonyl allenes has been realized by virtue of either N-phenoxy amides or N-enoxy imides simultaneously acting as the C- and N-sources, via redox-neutral tandem C-H activation/allene insertion/oxidative addition/C-N bond formation for the direct construction of allylamine d...
Article
ortho-Sulfonamide phenols represent a class of attractive structural motifs in medicinal and synthetic chemistry. Herein an efficient metal-free rearrangement reaction has been developed for the construction of ortho-sulfonamide phenols via HFIP-prompted intramolecular sulfonamide group 1,3-migration. This protocol features mild reaction conditions...
Article
Full-text available
The CpXRh(III)-catalyzed asymmetric cascade C-H coupling/intramolecular cyclization of azomethine imines with propargyl carbonates has been developed, affording a variety of chiral tetracyclic indenopyrazolopyrazolone frameworks with good substrate/functional group tolerance and enantioselectivity (up to 97:3 er). Combined experimental studies and...
Article
Full-text available
The experimental investigations on the catalyst [Cp*Rh(OAc)2 and Cp*Ir (OAc)2)]-controlled [3 + 2] and [4 + 2] annulations of oximes with propargyl alcohols have been finished in our previous work and a supposed dual directing group-mediated reaction pathway has been deduced for the chemodivergent product synthesis. However, the detailed interactio...
Article
Full-text available
Described herein is a Rh(III)‐catalyzed regio‐/stereoselective C−H coupling/C‐terminus Michael addition cascade of N‐phenoxy amides with 1,6‐enynes, giving access to bicyclic frameworks with the retention of the oxidizing directing groups. Thus, it also provides a straightforward platform for subsequent derivatization via two‐fold C−H functionaliza...
Article
Full-text available
Ortho -functionalized phenols and their derivatives represent prominent structural motifs and building blocks in medicinal and synthetic chemistry. While numerous synthetic approaches exist, the development of atom-/step-economic and practical methods for the chemodivergent assembly of diverse ortho -functionalized phenols based on fixed catalyst/s...
Article
A unique Rh(III)-catalyzed C-H activation/[3 + 2] annulation of N-phenoxyacetamides has been developed for the construction of dihydrobenzofurans via carbooxygenation of 1,3-dienes. This transformation features a redox-neutral process with specific chemoselectivity, good substrate/functional group compatibility, and profound synthetic potentials. A...
Article
An efficient and redox-neutral Rh(III)-catalyzed C-H activation/[3 + 2] annulation of N-phenoxy amides with propargylic monofluoroalkynes has been realized to afford 3-alkylidene dihydrobenzofurans with an interesting α-quaternary carbon center. Combined experimental and computational mechanistic studies revealed that a Rh(III)-Rh(V)-Rh(III) cataly...
Article
The Rh(III)‐catalysed C‐H couplings of 1‐naphthols with gem‐difluoromethylene alkynes have been realized for the direct construction of difluorinated dihydrobenzo[de]chromenes with broad substrate/functional group compatibility and good regio‐/chemoselectivity and in an atom‐economic manner. The unique fluorine effects account for the unconventiona...
Article
An unprecedented Rh(III)-catalyzed cascade C-H activation/Lossen rearrangement of aromatic amides with methyleneoxetanones has been realized along with a tunable C-N bond reductive elimination/trans esterification, giving divergent access to quinolinones and dihydroisoquinolinones via selective ring-opening of the four-membered lactone unit. Combin...
Article
Rh(III)-catalyzed, chelation-assisted oxidative C−H imidation of arenes with N−H imide have been realized using PhI(OAc)2 as an oxidant. This transformation exhibits a broad substrate scope and tolerates various functional groups. The reaction proceeded via in situ generation of an iodine(III) imido. DFT calculations suggest that this oxidative imi...
Article
Using gem -difluoromethylene alkynes as effectors, unprecedented diverse C-H activation/[4+2] annulations of simple benzoic acids are reported here. Remarkably, the chemodivergent reaction outcomes are well-tuned by Rh/Ir-catalyzed system; in the Rh(III) catalysis, 3-alkenyl-1 H -isochromen-1-one and 3,4-dialkylideneisochroman-1-one skeletons are a...
Article
An unprecedented divergent C−H functionalization of simple benzoic acids with gem‐difluoromethylene alkynes was realized in a controllable and chemoselective manner, which is tuned by RhIII/IrIII‐catalyzed system. The derivatization of obtained diene products and synthetic applicability on‐DNA synthesis were feasible. Abstract Using gem‐difluorome...
Article
Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted...
Article
A recent success in which the engineered iron-haem enzymes P411CHA′ aminate the intermolecular benzylic C-H bond with both high efficiency and stereoselectivity solves a long-standing challenge in synthetic chemistry (Arnold and co-workers Nat. Chem. 2017, 9, 629-634). The mechanism, reactivity, and stereoselectivity of this reaction were studied b...
Article
By using a synergistic dual directing group-assisted C-H activation strategy and simply modifying the reaction conditions, we realized a robust and general Cp*Rh(III)-catalyzed C-H cyclopropylation of N-acetoxybenzamides with cyclopropenyl alcohols, providing regio-, chemo-, and diastereoselective access to orthotrans- and cis-1,1-dimethylcycloprop...
Article
The cover feature shows a new and efficient rhodium(III)‐catalyzed redox‐neutral C−H activation/ring‐opening of strained ring/[4+2] annulation cascade of N‐methoxybenzamides with propargyl cycloalkanols, providing a direct access to diverse 3‐acyl isoquinolin‐1(2H)‐ones as potential anti‐lung‐cancer drugs. These antitumor agents can powerfully inhi...
Article
Full-text available
Peroxisome proliferator-activated receptor γ (PPARγ) is a key regulator of glucose homeostasis and lipid metabolism, and an important target for the development of modern anti-diabetic drugs. However, current PPARγ-targeting anti-diabetic drugs such as classical thiazolidinediones (TZDs) are associated with undesirable side effects. To address this...
Article
By making use of a direct C-H activation strategy, an efficient osmium(II)-catalyzed redox-neutral [4 + 2] annulation of N-methoxybenzamides with alkynes has been accomplished. Computational and experimental studies revealed that such transformation leading to the synthesis of the isoquinolone core might follow an Os(II)-Os(IV)-Os(II) catalytic pat...
Article
An enantioselective functionalization of the indole NH group is developed. The reaction stereo-selectivity is controlled by an N-heterocyclic carbene catalyst that adds to an aldehyde moiety at the C7-carbon of indole. The NH group participated in the carbene-catalyzed reaction is part of the heteroaromatic rings of the indole substrate. Our reacti...
Article
An efficient and practical Rh(III)-catalyzed redox-neutral [4 + 1] annulation of N-phenoxy amides with α, α-difluoromethylene alkynes has been realized to give direct access to the Z-configured monofluoroalkenyl dihydrobenzo[ d]isoxazole framework with broad substrate compatibility and good functional group tolerance, which was further enhanced by...
Article
An efficient synthetic route for the diastereoselective construction of trans‐dihydrobenzofurans via cascade [3,3]‐sigmatropic rearrangement/[3+2] annulation sequences has been developed. This protocol represents a metal‐free transformation of the promising N‐phenoxy amides with terminal alkynes and features mild conditions, good functional group c...
Article
The efficient couplings of diverse N-arylureas and methyleneoxetanones have been realized via Rh(III)-catalyzed and solvent-controlled chemoselective C-H functionalization, which involved the tunable β-H elimination and β-O elimination processes, thereby giving divergent access to quinolin-2(1 H)-ones and ortho-allylated N-arylureas with broad subs...
Article
Described herein is a Rh(III)-catalyzed and solvent-controlled double C–H functionalization of common benzamides via selective acyl C–O cleavage (β–H elimination) or alkyl C–O cleavage (β–O elimination) of the methyleneoxetanone substrate, which provides a straightforward way for the divergent synthesis of chain alkylated benzamides and seven-membe...
Article
Theoretical studies on DNA-cleavage and DNA-binding properties of a series of Cu(II) complexes [Cu(bimda)(diimine)] 1–5 have been carried out by density functional theory (DFT). The optimized structures of Cu(II) complexes were docked into parallel, antiparallel and mixed G-quadruplexes, with which the binding energies of complexes 1–5 were obtaine...
Article
As a cheap but harmful additive in food industry, 1‐phenylazo‐2‐naphthol (Sudan I) has attracted lots of attentions, which mainly focused on the determinations using the HPLC‐ESI‐MS/MS techniques. However, the fragmentation mechanisms are generally scarce. In this paper, the fragmentation pathways of protonated Sudan I in gas‐phase were investigate...
Article
The pyrrolotriazin derivative 2-(4-(4-((7-(3-(N-methylmethylsulfonamido)phenyl)pyrrolo [2,1-f][1,2,4]triazin-2-yl)amino)phenyl)piperidin-1-yl)acetamide (PPA) is a potential Janus kinase 2 (JAK2) inhibitor. The binding mode between PPA and JAK2 was investigated by using a combined method of docking, molecular dynamics (MD) simulation and binding fre...
Article
Benzofused nitrogen heterocycles are prevalent as key core structural motifs in functional molecules. Major syntheses of benzofused nitrogen heterocycles focus on the construction of the heterocyclic ring starting from (poly-)substituted benzene derivatives. Given that poly-substituted benzene derivatives are not always easily available, the flexib...
Article
Full-text available
A unique Rh(III)-catalyzed oxidative [5 + 2] annulation of easily available 2-alkenylphenols with propargyl carbonates have been developed by using two O-containing functional groups as the traceless assisting groups (AGs). The experimental investigations together with the density functional theory (DFT) calculations revealed that this transformati...
Article
Full-text available
As a major challenge in C-H borylation, how to control the selectivity has attracted lots of attention, however, the related mechanistic information still needs to be uncovered. Herein, density functional theory (DFT) has been used to study the mechanism for the ligand controlled regioselectivity in the iridium-catalyzed C-H borylation of aromatic...
Article
By virtue of a synergistically dual directing groups (the O–NHAc part and the hydroxyl group)-assisted strategy, the efficient and practical Rh(III)-catalyzed regioselective redox-neutral C–H functionalization of diverse N-phenoxyacetamides with propargyl alcohols has been realized, which led to the divergent synthesis of privileged benzofuran and...
Article
An efficient and redox-neutral synthesis of 2H-chromene-3-carboxylic acids from N-phenoxyacetamides and methyleneoxetanones has been realized via a solvent-controlled and rhodium(III)-catalyzed C–H activation/unusual [3 + 3] annulation sequence. This transformation represents the first example of using an α-methylene-β-lactone unit as the three-car...
Article
An efficient, mild and redox‐neutral iridium(III)‐catalyzed C‐H annulation of N‐phenoxyacetamides for the regioselective synthesis of benzofurans has been developed by employing tertiary propargyl alcohols as the versatile coupling partners. The computed results together with the experimental data revealed that the hydroxyl group of tertiary propar...
Article
Theoretical studies on DNA-cleavage properties of [Cu(bba)(diimine)] 1–4 have been carried out using density functional theory (DFT) and docking methods. The optimized structures of Cu(II) complexes were docked into DNA, glutathiones (GSH) and ascorbic acids (VC) so that the corresponding docking models were obtained. To explore DNA-cleavage proper...
Article
Group 9 Cp*M(III) (M = Co, Rh, Ir) complexes have been extensively investigated as catalysts in a variety of C−H activation reactions. Typically, late metal-based silver or copper salt was used (while needed) as oxidant in these catalytic systems. Herein, we report our discovery of a potentially general type of N-O bond-containing oxidants, which a...
Article
Fluorinated heterocycles play an important role in pharmaceutical and agrochemical industries. Herein, we report on the synthesis of four types of fluorinated heterocycles via rhodium(III)-catalyzed C-H activation of arenes/alkenes and versatile coupling with 2,2-difluorovinyl tosylate. With N-OMe benzamide being a directing group (DG), the reactio...
Article
A new core-double-shell microsphere [Fe3O4@SiO2@Zn(Por)OP] was designed and prepared by coating a core–shell composite of Fe3O4 magnetic core and SiO2 shell (Fe3O4@SiO2) with a zinc porphyrin-based organic polymer [Zn(Por)OP]. While, Zn(Por)OP was readily obtained by a convenient condensation of pyrrole and terephthaldehyde in propanoic acid follow...
Article
Density functional theory (DFT) calculations were used to study the mechanisms for hydrogenation of biomass-derived levulinic acid (LA) to γ-valerolactone (GVL) catalyzed by PNP-ligated (PNP = 2,6-bis(di-ter-butylphosphinomethyl) pyridine) iridium complexes, (tBuPNP)IrH3, 1. The transformation proceeds dearomatization/rearomatization including four...
Article
Titanate nanotubes (TNT) were found to be air- and water-tolerant, efficient, and recyclable Lewis acid catalysts towards the cycloaddition of carbon dioxide (CO2) to propylene oxide (PO) for the synthesis of cyclic propylene carbonate (PC). Using TNT as the catalyst and potassium iodide, tetrabutylammonium bromide or tetraphenylphosphonium bromide...
Article
A catalyst of palladium [Pd/MIL-101(Al)-NH2] supported on amine-functionalized Metal-Organic Frameworks (MOFs) allows selective hydrogenation of biomass-based 5-hydroxymethylfurfural (HMF) to 2,5-dihydroxymethyl-tetrahydrofuran (DHMTHF) with 2,5-dihydroxymethylfuran (DHMF) as an observed “intermediate”. The Pd/MIL-101(Al)-NH2 was prepared by using...
Article
The solvolysis mechanisms of RNA phosphodiester model 2-(hydroxypropyl)-4-nitrophenyl phosphate (HpPNP) catalyzed by mononuclear zinc(II) complexes are investigated in the paper via a theoretical approach. The general-base-catalyzed (GBC) and specific-base-catalyzed (SBC) mechanisms are thoroughly discussed in the paper, and the calculations indica...
Article
Density functional theory (DFT) calculations were used to study the mechanisms for hydrogenation of carbon dioxide catalyzed by the tetraphos-ligated (PP3: P(CH2CH2PPh2)3) cobalt complexes. We investigated the binding modes between CO2 and the cobalt metal center to determine whether the CO2 coordinated to the metal center in the catalytic processe...
Article
A new water-soluble ruthenium hydride complex [Ru(H)(bpy)2(PTA)]PF6 (bpy = 2,2'-bipyridine, PTA = 1,3,5-triaza-7-phosphaadamantane) (1a) was prepared. 1a reacted with CO2 and CS2 to give the corresponding formate and dithioformate complexes, respectively. Both the insertions of CO2 and CS2 into the Ru-H bond of 1a followed second-order kinetics. Th...
Article
Full-text available
For the application of functionalized metal–organic frameworks (MOFs) as a solid base, amine-functionalized MOF materials are achieved by (i) dative modification of unsaturated metal sites located at the secondary building units of MOFs with diamine, and (ii) covalent modification of the amine-tagged organic linkers within the MOF by alkylation wit...
Article
Full-text available
Density functional theory (DFT) calculations were used to explore the hydrolysis mechanism of the DNA analog BNPP (BNPP = bis(4-nitrophenyl)phosphate) catalyzed by the mononuclear zinc(II):OH− complex of 1,5,9-triazacyclododecane (Zn:([12] aneN3)). We present a binding mode in which one terminal phosphoryl oxygen atom as well as the nucleophilic gr...
Article
A mixture of [CpCo(CO)2] (Cp = cyclopentadienyl) and [Fe(pdt)(CO)2(dppe)] (pdt = S(CH2)3S; dppe = Ph2PCH2CH2PPh2) was stirred in refluxing toluene to give a heterobimetallic complex [CpCo(μ-pdt)Fe(CO)(dppe)] (2). The protonation of 2 with HBArF4 (bis-etherate of tetrakis[3,5-bis(trifiuoromethyl)phenyl]boric acid) in CD2Cl2 affords the μ-hydrido cat...
Article
Cyclohexanone is an industrially important intermediate in the synthesis of materials such as nylon and polyamides, but direct selective hydrogenation of phenol to cyclohexanone under green conditions is a challenge owing to the over-reduction of cyclohexanone to cyclohexanol. A catalyst made of palladium nanoparticles supported on polyaniline-func...
Article
Full-text available
The thermodynamics and kinetics for the binding of the potential anticancer complex [(η6-benz)Ru(en)(H2O)]2+ (benz = benzene, en = ethylenediamine) (1) to nucleotides under neutral and acidic conditions were studied by density functional theory (DFT) calculations, employing 5′-guanosine monophosphate (5′-GMP) and 5′-adenosine monophosphate (5′-AMP)...
Article
A systematic mechanistic study is reported for the aquation and nucleobase binding process of a series of Ru-II and Os-II arene-based anticancer drug complexes using density functional theory and COSMO implicit solvent model. The structures of Ru-II and Os-II complexes are similar to each other because of lanthanide contraction of osmium. However,...
Article
Full-text available
In this paper, the hydrolytic and aqueous solution chemistry of two half-sandwich Os(II) arene complexes [(eta(6)-p-cym)Os(pic)Cl] (1) and [(eta(6)-p-cym)Os(mal)Cl] (2) (pic = 2-picolinic acid and mal = maltolate) have been investigated using density functional theory (DFT). For aquation (substitution of chloride by H(2)O) of the complexes, three a...
Article
Density functional theory (DFT) calculations were used to study the mechanism for the cleavage reaction of the RNA analogue HpPNP (HpPNP = 2-hydroxypropyl-4-nitrophenyl phosphate) catalyzed by the dinuclear Zn(II) complex of 1,3-bis(1,4,7-triazacyclonon-1-yl)-2-hydroxypropane (Zn(2)(L(2)O)). We present a binding mode in which each terminal phosphor...
Article
Density functional theory (DFT) calculations at the B3LYP/6-31G(d,p) (LANL2DZ for Zr) level of theory were performed to elucidate the reaction mechanism for the reduction of amides to aldehydes using CP(2)Zr(H)Cl as a reducer. In Particular, a detailed study was done that involved a proposed iminium cation species in the reaction mechanism. Our cal...
Article
By means of the dual-level direct dynamics method, the mechanisms of the reactions, CH(3)CF(2)Cl + OH --> products (R1) and CH(3)CFCl(2) + OH --> products (R2), are studied over a wide temperature range 200-2000 K. The optimized geometries and frequencies of the stationary points are calculated at the MP2/6-311G(d,p) level, and then the energy prof...
Article
An investigation into the mechanism and stereochemistry of chiral lithium-carbenoid-promoted cyclopropanation reactions by using density functional theory (DFT) methods is reported. Previous work suggested that this type of cyclopropanation reaction may proceed by competition between a methylene-transfer mechanism and a carbometalation mechanism. I...

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